DAPPER GUESTS

A Story About Style & Personal Growth by Ollis Leander

Ollis Leander

21 August 2017

Ollis Leander Clothing QuoteI was once told that the greatest writers are the ones that write about getting up and telling you what they’ve seen in the toilet. Well, here is what I have seen.

My name is Ollis Leander Caudill. I am 28 years old and I currently reside in the area of Seattle, WA. I am an Active Duty member of the United States Coast Guard, a fitness fanatic, and a self-proclaimed men’s style and clothing aficionado. But first and foremost, I am a committed husband to my wife and a loving father to my children.

Growing up, I had a very interesting and unique life. I grew up in a rural area of central Missouri, outside of a small town called Steelville, population 900. I was raised by two loving parents, alongside five sisters. We lived in a large log cabin in the middle of the woods, miles away from civilization, on a hill overlooking the Meramec River. We didn’t have the typical luxuries afforded to us that most kids my age had, such as television and internet. I was care free and unruly as a child. Most of my hobbies consisted of roaming the woods and riverbanks barefoot, hunting, fishing, and chasing snakes and various other animals. All six of us children were schooled at home by my mother, while my father worked 24-hour shifts at the local hospital. We led a mostly isolated and sheltered way of life, with probably a less-than-normal amount of social interaction for children of our age.

Ollis Leander young

I experienced my first feelings of passion for clothing when I was about 14 years old. I was at a friend’s house and we were watching the movie Fight Club for the first time. When Brad Pitt’s character, Tyler Durden, appeared on the screen, I instantly became entranced with him. It’s hard to explain the feelings that captured my attention as I began to examine this man in the television set and the clothes that he was wearing; confusion, curiosity, desire, want, and perhaps even lust. Definitely lust. As silly as it may sound now, up to that point in my life I had never really considered the clothing that a man wore to be anything more than a necessity, a tool. A tool used to stay warm during cold months and to keep the sun off of one’s neck in the hotter months. Sure, I knew that it made girls look good and I loved to admire what they wore, but a guy… Why should anyone care what a guy wore, so long as it served its practical and functional purpose? You dress nice for church and certain social events, but the rest of the time why would you possibly give a damn what you were wearing? But nevertheless, as I sat cross legged on the floor staring intently into the screen, I knew that I had stumbled upon something that was going to change my life. Something that I could not shake. And as I began to examine this more thoroughly in my mind, I knew, almost instinctively, that I wanted whatever it was that the character of Tyler Durden was portraying through the clothes that he wore on his back. I wanted the look. I wanted the talk. I wanted his swagger. I wanted his bad-ass-don’t-care, look-or-don’t-look, I-am-who-I-am attitude. But most of all I wanted that beat-up, vintage, red leather jacket.

I spent the next few days at my friend’s house using his dial up internet connection to scour the internet, trying to find something that replicated the look I had seen and desired so much. I had no idea how to start, and even less of an idea of where to look. This was unchartered territory for me. Something I had not once before considered. I soon found myself overwhelmed and lost in a maze of blogs, forums, and websites. Everyone was telling me one thing here, only to go to the next webpage and be told the exact opposite. I was confused, and the only thing that I was certain of was that I suddenly wanted all of the things I saw but could never afford. I had opened Pandora’s Box. I had an old Suzuki Samuri that I decided to sell for $400, which I then spent on a “genuine Tyler Durden Fight Club” leather jacket from a sketchy website that I could never seem to find again. Weeks later, when the package finally arrived, I was ecstatic! I couldn’t wait to get it up to my bedroom so I could open it in private. I was slightly embarrassed, and very unsure, and my family had no idea what I was up to. This was it. This was the jacket that was going to change my life. This was what was going to make me look the part, walk the walk, talk the talk. It was the answer to all of my newly acquired obsessive dreams and wants that I had so quickly developed during the past few weeks. Much to my dismay, the jacket was huge. I hadn’t realized that I would need to order the right size for me. I knew nothing about size. Call me ignorant, but I didn’t even realize such a thing existed. I don’t know if it was real leather or not (I would guess not), but it was far too big and it fit me nothing like it did Brad Pitt’s character. I was heartbroken. I felt cheated, betrayed and abandoned by a materialistic promise that was supposed to make all of my adolescent dreams come true. I felt devastated. But, nevertheless, I pushed. I spent any money that I could manage to scrape together on any clothing items from small local department stores that I thought might make me look like what I had imagined.  And might emulate what I saw online and in the GQ magazines that I saw at the super market. I looked ridiculous, and in turn I was ridiculed. Friends laughed at me, my sisters teased me, girls laughed at me. Maybe it was because of the rural community that I lived in. Maybe it was because I had bad friends. Maybe it was because sisters just tease mercilessly. Maybe it was because I was wearing a giant red leather jacket with my hair spiked straight up. Either way, I became angry, and then I became embarrassed. My materialistic dream that had promised so much, for the second time in a short time span, left me out to hang high and dry. I felt as though I would not recover from the let down. During this same time in my life, my parents separated and my mother moved into the local town, completely changing the dynamic of our family. Being homeschooled, and growing up in such a close-knit household with such close relationships and loving parents, it was like an earth-shattering quake rippling through our family, and it left me broken and devastated. Although my sisters and I continued to stay close to one another and to both parents, it rocked my world, and in turn I rebelled. Although the passion that I had so briefly felt never really left me, I suppressed it and any dreams or ideas to look like what I had so deeply imagined; shoving it down to the bottom of my heart, into a closet of broken and failed dreams, and I locked the door. Instead, I spent most of my time helping my father in maintaining the house and daily chores, and assisting in the care of my two younger sisters in the absence of my mother.  And when my friends started skateboarding, I immersed myself into the culture of punk-rock. I grew my hair out, wore baggy, ripped jeans, tattered t-shirts, and black flannel shirts. I found a certain amount of solace in the skateboard and punk-rock culture, as it gave me freedom to express myself visually while still allowing me a place to feel like I fit in. But it still never fully satisfied the lingering feeling left from my yearning that would continue to present itself every time a GQ would happen to catch my passing glance. During this time I also discovered alcohol, which I quickly learned helped me cope with the pain and loss that I had began to experience. Little did I know that alcohol would become the foundation that I would build my young life on, and that I would continue to abuse as a coping tool for many years to come.

Ollis Bike

When I turned 18 I left home, leaving my father and two younger sisters to fend for themselves. I took to the road and soon found myself in Northern California. I settled on top of a hill overlooking Monterey, working minimum wage at Bubba Gump’s Shrimp Factory, and paying $850 a month for a bed in a strangers’ garage. Here I discovered the surf culture: bleached-out shaggy hair, golden tan skin, the ocean, and marijuana. Much like the skate punk culture, I found the freedom to express myself visually while still belonging to something. I spent the next year surfing, smoking, drinking, and forgetting about the world. However, mostly due to a lack of funds, my time there soon expired and I found myself feeling vacant, lonely, and uninspired. So I decided to pack up and move back to my home state. This time, I headed to the south end of the state in the city of Springfield, with the intent of enrolling in the state college there.

I ended up only taking one college class, a summer class at that. I hated it. I hated school. Blame it on my upbringing. Blame it on my lack of structure. Blame it on my drinking. Blame it on my attitude. Regardless, I knew I wouldn’t be able to perform the duties of a full time college student, and I had no idea of what to go to college for anyway. By this time, my dreams of men’s style and fashion were collecting cobwebs in my heart, and I had no real idea that you could even attend school for such a thing anyway. Instead, I enrolled in a local firefighting and EMT program, while working night shifts waiting tables at the local Olive Garden. Here I met my wife, Heidi Lynn. She was a Missouri State student, pursuing her degree in elementary education while working as a hostess at Olive Garden. She was gorgeous. I wish I could say it was love at first sight, but it wasn’t. I was simply lonely and horny. I asked her out, only to promptly be turned down. But I continued to persist, and I finally landed a date with her. She was nothing like I thought she would be. She was a “good girl”, very proper and well raised, and I quickly realized that this was not going to be a girl that I would end up taking home with me that night. Instead, after two years of dating, we were wed on March 5th, 2011 at the local church that we attended. We moved into a small, one-bedroom apartment beside a golf course. She was in her last year of school, and I was still waiting tables and attempting to become a local firefighter or EMT first responder. I was now 21, and with the freedom to purchase my own alcohol, my drinking began to escalate. I began drinking heavily on a nightly basis. I wasn’t out roaming the town partying or getting in to trouble, but nevertheless, it was becoming a strain on my relationship and to my new bride.

Ollis Leander Tartan

In 2012, at the age of 22, I enlisted in the United States Coast Guard. My efforts at becoming a firefighter had fallen through, and like most failures that I encountered, I counted it as loss and gave up, shoving it into my closet of lost and broken dreams. Heidi had graduated school, and we were beginning to talk about having a family. I knew I needed a job that would enable me to provide for a family, and the idea of serving my country had always appealed to me. So, off to boot camp I went.

The Coast Guard was nothing like what I had expected. After boot camp, I was assigned my first duty station in Seattle, WA aboard the Coast Guard Cutter Mellon- a 378′ sea-going vessel with 170 members on board, with the primary mission of patrolling the South Pacific for drug runners. My duties aboard the ship included the tedious, low-ranking work such as painting, chipping paint, scraping rust, and sweeping, as well as the the overall maintenance of the decks while underway. Although grateful to have a job, I was miserable aboard the ship. During my first deployment, my drinking habits increased even more during the various port calls. I drank heavily during the few days in port at foreign destinations in order to cope with my stress and displeasure of life on board a ship, and being away from my wife. It was easy to do because I was now in an environment where everyone drank excessively at port calls. It was the norm, expected, and almost promoted in ways. I never thought twice about my increasing habit; a habit that only continued to worsen even when I was back at home.

Ollis Floral Tie

As dissatisfied as I was with life on the ship and my current and minute role in the Coast Guard, I decided that I was bound and determined to become a helicopter rescue swimmer. I was in great physical shape at the time, and I wanted something that would really challenge me. The Coast Guard’s Aviation Survival Technician School is one of the hardest programs that the military has to offer, and boasts the highest attrition rate of all of the special operation training programs. I decided that this would do. I would make a career saving lives and I would be a hero! Having grown up on a river, I was very comfortable in the water, and I was very comfortable with being daring, so it made sense to me.

I was accepted into the school in October of 2013, just seven short weeks after the birth of our now 3 year old daughter.  I left home, once again, to attend the 24-week course in Elizabeth City, NC. The school was grueling. Far worse than I had anticipated, and much, much harder than I had imagined. I started the school alongside 30 candidates, and after only a few short weeks I found myself standing alongside only 6 men. Guys had gotten hurt, they had quit, they had gotten scared, and they had failed. But that wasn’t going to be me. I knew it. I excelled in the school. Although I had no training in proper swimming techniques, I adapted and learned quickly, surpassing some of the better men that our class had started with. I studied and I trained. I even trained at the local swimming pool during the weekends on my off days. Also on the weekends, I would continue to drink myself into oblivion in order to deal with the stress and homesickness. Sometimes I drank so much that I could barely stand straight for Monday morning PT at 4:30 am. But my sheer determination pushed me on. I was in week 18 when I sustained the injury. I had damaged the nerves and soft tissue in my left foot, and it had swollen to the point where I could no longer squeeze my boot on. It writhed with pain and was purple and blue. I had lost all feeling in my toes. The doctor deemed me unfit to continue, so on March 2nd, 2014 I was un-enrolled from the Coast guard’s AST “A” School program. I was crushed. I drank.

Ollis Leander Grey Jacket

I was sent back to Seattle, WA to the ship, and to my wife and child. I continued to work on the ship for several weeks until I was accepted to school to become a “Yeoman”, the Coast Guard’s version of Personnel and Human Resources department. It was nothing I had ever imagined myself doing, but I figured the change of pace might be nice, and I wanted off of the ship and to be promoted. So, once again, I left my wife and our now 6 month old daughter, this time to the Coast Guard Training Center in Petaluma, CA. I hated Yeoman school. It was everything that I never wanted to do with my life; sitting at a desk, punching keys for meaningless reasons that I didn’t understand. I was irate that my body had failed me, and I was angry at the world. I didn’t get along with most of my classmates and in turn, my drinking sky-rocketed. There was a local bar on base, so alcohol was easily accessible, and I drank to my heart’s content on the weekends and on most week nights too. Twice I was almost un-enrolled for disorderly conduct, but I scraped by and finally graduated the seemingly never ending 8 week course. After school I was stationed back in Seattle, but this time at a Coast Guard base on land.

Office life was as easy as could be for me. Although I had distaste for my job, I found that I had a talent for it, and I was well liked by my supervisors. I soon excelled, promoting twice in just one short year of being there. I had also discovered that since I was working a 9 to 5 job, and the fact that I could do my job in my sleep, I could drink whenever and however much that I wanted to. I spiraled out of control. Although I was performing well at work, I had a dirty little secret and my home life was a wreck. My wife had lost all but her last ray of trust for me, I was neglecting to pay much attention to our baby girl, and I was selfishly blowing copious amounts of our hard earned money on booze. I was drowning. I was drowning in a pool of Tennessee whiskey and my own self pity. But then, in one night, it all changed.

Ollis Leanders blue jacket

Call it a miracle, call it an epiphany, or call it God. Call it whatever you like, but after almost 15 years of drinking away any feeling and emotion I might have had, I woke up after a three-day binge and I knew that I could never touch another drop of alcohol again. I knew that I was going to lose everything I had ever loved if I continued to go down the road I had been walking. I knew my wife would leave me, that I would lose my job, and that I would die drunk and alone. I was scared, and I knew that I needed to change…had to change. That morning I arrived to work at Coast Guard Base Seattle scared out of my mind. Not knowing where to turn, I walked straight into the Chaplain’s office and the only words that I could get out of my mouth were, “Sir, I’m an alcoholic, I don’t know what to do and I need help.” And on June 30th, 2015, after a medical screening, I was self-admitted to inpatient treatment for alcoholism.

30 days later when I emerged from treatment, I was riding on a pink cloud. Everything was great; everything was going to be fine! I had fixed myself, and life was going to be grand. Or so I thought. After only a few days at home, although still sober, I found myself in a deep depression, completely empty… lost. I had nothing. I felt has though my best friend had died and I had no one to turn to, and nothing to look forward to at the end of each day. I realized that I knew nothing about myself. Everything I had set out to do had always ended in drunken stupor, and now that was gone. I did not neglect the fact that I had a loving wife (who was now 7 months pregnant with our second child) and a beautiful, healthy two-year-old girl. But for myself, I had nothing. I loved to work out, but fitness had always been more about maintaining a healthy lifestyle to me, not a hobby, and certainly not a passion. I had a void in my life, and I had no idea of how to fill it.

And this is where my story actually begins.

Ollis Leander Insidewall

It all started with the shoes. A pair of brown oxford shoes to be exact. A few weeks after arriving home from treatment, I was musing through my closet trying to find something good to wear to church. My wardrobe, in all of my drunken stupor, had been badly neglected, and I was irritated that I could not find anything to my liking. Even more irritating was the fact that, aside from a few tennis shoes and a pair of boots, the only other real pair of shoes that I possessed was a pair of black, square-toed derby shoes that I had worn for my wedding years before. And I loathed them. I told my wife that I wanted to buy a pair of brown shoes, and that I couldn’t understand why I didn’t own a pair already since brown was so much more versatile than black. Because I am not a person who makes a purchase without thoroughly investigating the product (something I had learned long ago when I was young), I turned to the internet one day at work to begin the hunt for a new pair of dress shoes, ones that I could afford. Almost instantly I was 14 again, sitting in my friend’s bedroom, overwhelmed with options, opinions and brands upon brands that I had no understanding of, and that of which I could not decipher. But this time, something different happened. Instead of becoming discouraged, confused, and irritated, I became intrigued. I spent the rest of that day reading any and all information I could find pertaining to men’s footwear. And there was a copious amount to sift through. During the rest of my afternoon at work, I read about the basics: the difference between balmorals and bluchers, brogues, cap toes and wingtips. I read about the history of each type of shoe, how to tie laces on the different shoes, how one should match different shoes to different ensembles, leather care, shoe trees, construction, and the list goes on. The next day I went on to research hundreds of brands and manufacturers, as well as reading any and all reviews of each one. And I didn’t stop there. Suddenly, that feeling that I had felt so long ago while sitting on the floor watching Tyler Durden swagger in his red leather jacket and his “sock it to me” t-shirt began to resurface; the excitement, the want, the lust, the passion. It was all there again. With a rush, I suddenly realized that this was it. This was the key to my missing piece, to fill the void. This was my passion. The idea of being able to create my own self image, an image of what I wanted to see and how I wanted to be, and the idea of being able to visually portray my feeling on my sleeve, literally, provided me with a warmth and tingling sensation that I can only describe so nearly as love. I continued on. I read. Suits, sports coats, shirts, trousers, and ties. Knit wear, socks, pocket squares. By the end of that week I had decided that I didn’t want a new pair of shoes, I wanted an entirely new wardrobe. One that I liked. One that I loved. One that I could touch and feel. One that my personality and creativity defined, and that spoke without words about who I was. I divulged myself into websites geared toward men learning how to dress like men in quality affordable style; websites such as Dappered, Primer, and Art of Manliness. I read about it all. I read everything. I got on forums and I asked every question I could think of. I absorbed it all like a dry sponge to water.

At first I wanted to build a basic, staple wardrobe, one that was versatile and made sense. Two suits, one navy and one charcoal. A navy blazer and gray slacks. Black balmorals, brown bluchers, a navy grenadine tie, and some basic accessories.

Ollis street

I became completely obsessed. Over the next couple of months I began to research and retain copious amounts of information regarding menswear. I had my entire wardrobe mapped out on paper. I had everything chosen for the perfect and completely functional wardrobe. I began tracking sales of hundreds of brands religiously. I went to stores to see things in person, to touch and feel, and to try on, in order to be able to make more informed decisions. I learned measurements, and I learned my measurements. What cuts I wanted, what fit I wanted. I had all of the correct information, all the details planned out. Where I would buy items from, what order I would make purchases in, in order to keep my new wardrobe running as smoothly and as versatile as possible. On paper, I was already done. It was perfect. Or so I thought. All of this learning, effort, and researching, and yet I realized, I felt reluctant to actually purchase anything. I finally bought a mid-lower end navy suit, like I should. I returned it immediately. I bought a charcoal suit instead, and a navy blazer. I promptly returned both of them. I began to wonder what was wrong with me. This is what I had wanted, my ideal wardrobe. I began to become discouraged. Something wasn’t fitting, and it wasn’t just the clothes. I wanted what I saw other men wearing. I wanted their uniqueness, but I knew in order to start, I had to start with the basics. But whenever I would buy a “staple” item, I felt unpleased, unenthused, and almost bored. No, I definitely felt bored. This wasn’t what I saw the men that I so much admired and aspired to be like wearing. This was what everyone else wore. But surely these men I idolized started with the basics, right? A solid suit, brown oxford shoes? And then, it dawned on me. Like a ten ton of brick falling from a window onto my head, it dawned on me. I didn’t want a versatile, basic wardrobe made up of so called “staple” menswear essentials. I didn’t want a charcoal suit. Hell, I didn’t even want a suit! Why would I even need a suit? I spent the vast majority of my day confined to the walls of an office, bearing the uniform of my chosen service. There was really only two days out of the week that I really even wore anything else, aside from leisure-wear around the house. Aside from the occasional wedding, and god forbid, funeral, I had nowhere to even wear a suit to. No, I wanted to be free. I wanted to dress how I had imagined when I was a 14-year-old boy watching Tyler Duren. IMAGINE. That was how I wanted to dress. From my imagination, how I felt, how I wanted to look. Not like other guys, but like a blank canvas just begging to have life breathed on to it. I soon realized that the opinions of the internet and of so many others on there had gotten the best of me, now and before, and had held me back. I had become so completely immersed in “doing things right” and what other people might think, that in just a few short months I had already lost the passion for what it was that I was after in the first place. I wanted that lust. I wanted to be able to open my closet doors and not see an ocean of blues and grays, but of color and texture and life. Pieces of clothing that spoke to me, and spoke for me. That I could create with and wear how I felt. And why shouldn’t I? I was 28 and married with children. I literally had nothing to lose. I took my list that I had so painstakingly composed and tore it in half and threw it in the trash. I was free.

I turned back to the internet, but this time I forgot everything I had just learned. Instead I followed my heart and my passion. I did buy a blazer, my first. But I bought it in a bright blue hopsack. I also bought a few white and blue shirts, and some solid slacks and a pair of brown oxfords. But that’s where I stopped. I then turned to bold plaids, checks, stripes, and tartans. I discovered suede and monk straps, boots and scarves. Bright, colorful ties and pocket squares. I stopped worrying about people on style threads. I stopped caring what the websites said. I started only caring about what I felt about something, and how it felt upon my skin…how it made me feel and look. I had arrived. I had bliss.

Ollis Leander sweater

Clothing has taught me to be less concerned with the world, and more concerned with myself and my well being; something that I did not often practice before. The void that I once felt is now overflowing with a river of colors and patterns. It has placed a selfish joy in my heart, something for me. Something that I can safely say I had never had up until this point. Clothing is more than a hobby to me. It is my joy. It is my passion. It is how I express when I’m happy, sad, or angry. How I express my achievements and failures. My role in my family, and my role in society. It gives me purpose. I now look forward to each day after work, and each weekend. I wait all day at work for the moment when I arrive home and paint my blank canvas, a new creation each and every day.

I have pursued my passion for men’s clothing steadily for the past couple of years, and in order to not count myself as ignorant, I continue to learn. In my mind, I will never be done learning, nor will I ever be able to learn enough about men’s style. I learn something new each and every day. I am always reading and researching, asking questions, trying something new. I am always just beginning. My focus, instead, has gone from the opinions of so many on the internet, to focus on fit quality, and myself. I pride myself on being able to buy clothes of the highest quality and fit for the best possible prices for my modest budget.

Today, after two years, I am proudly still abstinent from alcohol, and I have come to the realization that if I wish to continue this path in seeking what I am truly passionate about, that I will have to create it to be my main focus and my choice of career. This was not a decision that I have taken lightly, as I have my family’s stability to think of first and there is a lot of risk involved. However, I can now hear my calling clearly, one that began voicing itself so long ago, and as I was once told, “you have to put on your oxygen mask first before you can help others.”

So here I am…a 28-year-old man with a career, a wife, and two kids. Ready to change. Ready to sacrifice. Ready to begin this new chapter in my story.

“What man actually needs is not a tensionless state but rather the striving and struggling for some goal worthy of him. What he needs is not the discharge of tension at any cost, but the call of a potential meaning waiting to be fulfilled by him.”  – Victor Emil Frankl

You can follow Ollis on his Instagram

GEORGE CLOONEY LOVES MY STYLE CONSULTING SERVICES. YOU'LL LOVE THEM TOO!



FREE Updates+ FREE E-book!

Are you serious about reaching your style goals? I'm serious about helping you get there!

Join to receive free updates and download a copy of my E-book "8 Days, 8 Steps To Improve Your Style" completely free!

NO SPAM. FOR REAL.

You have Successfully Subscribed!

JOIN THE EXCLUSIVE FACEBOOK GROUP

DRESSING UP IN A DRESS DOWN WORLD

JOIN NOW!

You have Successfully Subscribed!

Pin It on Pinterest

Share This